


Tell Me I'm Pretty

by thatwriterlady



Category: Supernatural
Genre: College Student Dean, Fluff, Funny, Gabe ships it, M/M, Matchmaker Gabriel, Pizza Man Dean, Professor Castiel, Professor Gabriel, just cuteness, lots of cuteness, prompt
Language: English
Status: Completed
Published: 2016-02-25
Updated: 2016-02-25
Packaged: 2018-05-23 02:23:13
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 5,626
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6101635
Author URL: https://archiveofourown.org/users/thatwriterlady/pseuds/thatwriterlady
Summary: <blockquote class="userstuff">
              <p>Gabriel decides to order pizza for him and his brother one night.  He has an app on his phone and after he orders the food he sees there are directions he can write in for the delivery driver.  Really, he does it as a gag.  He asks the delivery guy to tell him a joke.  The guy actually comes through.  The guy also turns out to be one of his senior year students at the university, a good looking guy by the name of Dean.  He decides he not only likes the pizza, but he likes Dean's friendliness outside of the classroom.  It becomes a running joke to order on nights Dean is working just to put silly requests down in the instructions box.  Until one night he is stuck in the bathroom and leaves his brother Cas to answer the door.  Gabe had added a request that night.  <em>Tell me I'm pretty</em>  </p><p>As always, Dean follows through with the instructions.  Too bad no one let Cas in on the joke.</p>
            </blockquote>





	Tell Me I'm Pretty

**Author's Note:**

> Don't worry, Cas is a good sport here! And this was all in good fun! It's a PROMPT. I'm wary of doing prompts now because of the negativity on past stories, but this felt like a cute one to do. I do hope you all enjoy it!

[](http://www.pizap.com/image/707476471pizapw1456358535.jpg)  
[](http://www.pizap.com/u/707476471) on [piZap.com](http://www.pizap.com)

 

Thank you, Cassie, you have no idea how much this means to me, you letting me stay with you. I swear I’m looking for my own place. There’s a nice building across the street that has a unit opening up, but not til September. I’d like to grab it; I already took a tour and it’s really nice, but…” Gabe fiddled with the pen in his hand as he looked across the table at his younger brother. He was starting to feel like he was overstaying his welcome. Gabe was the new anthropology professor at the university, having come to work alongside his younger brother there, and not properly planning ahead (it was his curse), he had arrived in the city with absolutely nowhere to stay. Cas had graciously taken him in. That had been in May. It was now July.

“It’s fine, if that’s the apartment you want, September isn’t that far away. It’ll give you the time you need to put down the security deposit so the landlord doesn’t rent it to someone else before you can get it,” Cas assured him. He didn’t mind his brother staying with him for a couple of months. Gabe had offered to pay half the rent while he was here, so there were benefits to him staying.

“You’re the best. I was thinking, how does pizza sound for dinner? I have an app on my phone and we can just order one, kick back after we’ve finished grading all of these papers and watch a little of that show you like, Dr. Sexy,” Gabe said. Cas smiled. He did love pizza…

“Alright, get one meat lovers.”

Gabe was already pulling the app up on the phone. “You got it.”

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

While Gabe had the app on his phone, he’d only ever ordered a pizza once with it. It took him a moment to pull up the coupons and go through them to see there were any they could use. He decided on a two mediums for $5.99 each would work, so he ordered two of them and some breadsticks stuffed with spinach, mozzarella, and feta, simply because they sounded _really_ good. The actual ordering wasn’t hard at all. Ten minutes later he had two pizzas, an order of the breadsticks, and lava cakes loaded into his cart. He filled in his card information and placed the order. It took him to a new screen where it gave him the option to leave orders for the driver. Being the smartass that he was, he left instructions in the box.

_I want the driver to tell me a funny joke_

With a smirk he pressed enter and exited out of the app. He was hungry and the pizza couldn’t get there soon enough.

 

“Dean! You’ve got a delivery!” Jo yelled. Dean had been leaning against the counter talking to Benny when he heard his name. He stood up straight and accepted the stack of boxes, slipping them carefully into his insulated bags. 

“Later, Benny,” he said as he started for the door.

“Later, Brother.” Benny gave a little wave as Dean left.

Out at the car, Dean took a moment to look at the actual order. It was going to one of the apartment complexes near the university. He frowned. The university students could be real asses when they wanted to be, and they tipped like shit. With a silent prayer he set the bags on the passenger seat and slid in behind the wheel of his car. One last look at the order and he noticed that one of the boxes that was almost never filled in, it had writing in it.

_I want the driver to tell me a funny joke_

Dean arched one eyebrow. They wanted him to tell them a joke? Shit. It was definitely a college student. With a few curse words mumbled under his breath he pulled out of the parking lot and started the drive. Silently he prayed they would tip at least a couple of dollars.

~~~~~~~~~~~~~~~~~~~~~~~

The drive was short and Dean knew shortcuts so five minutes later he was pulling up in front of one of the nicer buildings in the area. He got out, taking the bags with him, and climbed the stairs to the second floor. Apartment 2B was the second door on the left, and he stepped up to it and knocked firmly.

“Cassie! Pizza’s here!” a man yelled. A moment later the door was being opened and Dean found himself staring at a strangely familiar face. The man had a lollipop stuck in the corner of his mouth. Amusement danced in his amber eyes as he looked Dean over.

“Well _hello_ , Handsome!” He waggled his eyebrows in what Dean assumed was flirtation, but all he could do was snort and roll his eyes.

“Did you order the meat lovers, a Hawaiian with extra pineapple, spinach and feta breadsticks and lava cakes?” he asked. The man nodded eagerly.

“Hell yes!” The man watched as Dean carefully slid the boxes out of the bags and handed them over. “Do I know you?” the man asked. Dean looked up at him, studying him for a moment.

“Wait…yes, I didn’t recognize you without the slicked back hair and glasses. You’re Professor Novak, right? I’m in your third period anthro class,” Dean replied. So not a cheap college student. He was delivering to a professor. He hated passing judgment on his fellow classmates but seriously, they tipped like shit, even to their own.

“Right…Dean, is it?” Gabe asked. Dean nodded.

“That would be me.”

“It’s quite interesting to hear your side of the debates in class. It’s refreshing. I wasn’t sure when I moved here whether I’d fit in or not, but so far, I like it,” Gabe said. Dean preened a little at his professor’s praise. Anthropology was his favorite class this semester.

“I hadn’t realized you were new to the university. How are you and your wife liking the area so far?” Dean asked. Gabe squinted in confusion.

“Wife? I’m not married. Not even in a relationship.”

Was…his professor flirting? Well that was a little weird. Beyond that, Dean was embarrassed to have assumed anything. “Oh, sorry, you just…I heard you call out to a Cassie when I knocked…”

The confusion disappeared completely and Gabe smiled warmly. “Ah, no. Cassie is short for Castiel, my younger brother. I’m staying with him until I can get a place of my own. He’s a professor at the university too.”

“Oh, sorry about that,” Dean apologized. He handed the receipt to Gabe to sign it. When he handed it back there was nothing marked for the tip. Great, his professor was a cheapskate too. He sighed internally and started turning to walk away.

“Wait, don’t you want your tip?” Gabe had set the boxes down somewhere Dean couldn’t see and had his wallet out. He turned back to the man. Gabe pulled a ten out of his wallet and looked up expectantly at him. “Well?”

Dean frowned. “I’m sorry?”

“A joke. You’re supposed to tell me a joke. Do the drivers usually not read delivery instructions?” Gabe asked. Dean’s eyes widened in realization.

“Oh! No, we read them. I’m sorry, I just forgot. You really want a joke?”

“I most certainly do. Come on, make me laugh.” Gabe crossed his arms and waited. Dean’s mind went completely blank.

“Uh…” He was blanking on all jokes, except the one he’d heard last night in one of his video games. It wasn’t _that_ funny. He hoped it would suffice.

“What does a vegan zombie eat?” he asked.

There was renewed amusement in the professor’s eyes. The corners of his mouth twitched as he tried not to smile before he heard the punchline.

“I don’t know, what do they eat?”

Dean held up his arms in front of him like a zombie reaching out to eat someone and groaned out: “Graaaiiiinnnsss!”

Gabe blinked and his mouth fell open. Then he was laughing. “Oh, now there’s one I’ve never heard before! I like that!”

Dean dropped his arms and grinned. “I got it from one of my video games.”

“Which one?” Gabe asked.

“Dead Rising Two. I just beat it last night.” 

Gabe smirked and nodded. “I like those types of video games. I’ll have to try playing that.”

“It’s long and there’s a lot of B.S. but it’s still a fun game,” Dean said.

“I’ll keep that in mind. Are, uh, you always on this route?” Gabe asked.

“I work Tuesdays, Fridays, and Sundays, so this is my route on those days,” Dean confirmed. Gabe smiled wide again.

“Good to know. We’ll be ordering again soon from you. Have a great night, Dean.” 

“Thanks, Professor Novak, you too.” He accepted the money the teacher gave him and started for the stairs. Now, if all of his tips tonight were this generous he wouldn’t need to work as hard as he did. He needed the money though. Tucking the money into his pocket, he hummed happily all the way back out to his car.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

“Oh, Cassie, Cassie, Cassie…” Gabe sighed dramatically as he carried the boxes into the kitchen and set them on the table. Cas looked up from the papers he’d been grading.

“What?”

“The delivery driver was _delicious_!” Gabe’s grin was wicked. The corners of Cas’ mouth twitched up into a not quite smile.

“Did you flirt?” he asked.

“Alas…no. He’s one of my students. Senior year, government major if I remember correctly. Much too young for me. But for you…” Gabe sat down and opened the box of lava cakes. He pulled one out and bit into it. A long groan escaped his lips as he chewed.

“He’s really beautiful. Infinitely more attractive than anything you’ve ever dated,” he added once he’d swallowed. Cas snorted and reached for the box of breadsticks.

“What are these?” he asked as he opened the lid and peered in.

“Stuffed breadsticks. They have mozzarella, feta, and spinach. Let me know if they’re good.” Gabe cleared off his lava cake and reached for another. Cas broke off one breadstick and opened a little cup of marinara sauce. Careful not to make a mess, he dipped the bread and took a bite.

“Oh! These are fantastic!” he exclaimed.

“Good. I definitely plan to order more often from this place, even if only to see Dean more often outside of the normal school setting.” He found himself wondering if Dean even liked men. Across from him Cas was working on a second breadstick. Cas was twenty five and had barely dated since he’d started teaching. From what little bit he knew of Dean from class, the man was vibrant, intelligent, and funny. Just what his brother needed. Yes, they would definitely be ordering from that pizza place much more often.

~~~~~~~~~~~~~~~~~~~~~~~

It was two weeks later, another Tuesday that Dean found himself delivering again to the Novak residence. Same order, except this one included a second order of the breadsticks. Well, _someone_ sure liked those! As he climbed into the car he remembered the delivery instructions from the week before. A quick check of the instructions on this order showed there were new ones.

_Show me your favorite dance move from the 80s_

“Seriously?” Dean laughed and shook his head. Professor Novak was definitely his favorite teacher. The man was entertaining and got the entire class involved. He just had so much energy it was incredible. It was going to be a shame when he left this job at the end of the summer. He was graduating, and there was a history position waiting for him at the high school. He’d be teaching history and government. It was a dream come true, and he couldn’t wait to start.

The drive to the apartment complex was again short, and he hummed to himself as he climbed the steps to the second floor. When he reached the apartment he knocked. 

“Cassie, can you get the door?” He heard Professor Novak yell.

“I can’t! I’m in the bathroom!” a faint voice called back. Dean snickered. It reminded him of himself and his own brother, Sam. He waited patiently and about thirty seconds later he heard footsteps approaching. The door flew open and he found himself standing face to face again with his professor. The man looked thoroughly pleased to see him.

“Dean! Good to see you!”

Dean smiled and nodded. “Well, you _did_ order from us.”

Gabe laughed and nodded. “Cassie absolutely loves the stuffed breadsticks. Ate almost the entire thing himself last time, so I got extra this time so I could get a couple.” 

“They’re really good,” Dean agreed. He and Sam sometimes forewent ordering pizza and just got a couple orders of the breadsticks for that reason. He removed the boxes from his insulated bags and handed them over. Gabe set them down somewhere out of sight and turned back to look at him.

“You want my favorite dance move, right?” Dean asked, unable to hide his grin.

“You got it, Dean-o.” Gabe’s grin was wider.

“Well…” Dean thought for a moment. He didn’t really dance, but there were some funny ones that made him laugh. Setting his bags momentarily on the floor he hooked his thumbs in the waistband of his jeans and launched into a very clumsy M.C. Hammer’s “Hammer Dance.” Gabe clapped excitedly, thoroughly delighted by his choice of dance. Dean stopped and grinned as he ducked down to pick up his bags.

“ _That_ was totally worth it!”

“I always thought that one was kind of fun,” Dean admitted. Gabe nodded as he pulled another ten out of his wallet and handed it over.

“It was. It’s a shame he faded away. He had potential.” 

“I only know like, one song,” Dean said. Gabe nodded.

“How old are you, if I might ask?”

“Twenty two. I should have graduated last year, but I missed a semester cause my mom got sick,” Dean replied.

“Hey, you do what you have to do. You’re getting your education and that’s what matters. You’re a government major, right?”

Dean was impressed that his professor remembered that with as many students as he had. He really hoped the man wasn’t interested in him in ways that were outside of a school setting. While Dean liked men and dated them, his professor wasn’t exactly his type.

“Double major, actually. Education and government. With a minor in history.”

“That’s quite ambitious. You and my brother would get along splendidly. He got his degree in education and history. He teaches three different history classes this year,” Gabe said.

“I have a job lined up at the high school. I graduate end of next month, and then I start my new job two weeks later. I’ll only work this job on weekends then, until I get a couple of paychecks under my belt. Then I’m quitting.” Dean had a plan. 

“Good for you! I like seeing my students succeed. This is Cassie’s second year teaching. He’s a young’un like yourself,” Gabe chuckled. Dean smiled. 

“I hope he likes it. I know I will.”

“He does, he loves it.” Gabe tucked his wallet back in his pocket. “Well, I will see you tomorrow in class, and we will certainly be ordering again very soon.”

Dean smiled politely and nodded. “You have a great evening, Professor.”

“You too, Dean.”

~~~~~~~~~~~~~~~~~~~~~~~~~~~~

“Mmmm, did you get the breadsticks?” Cas asked when he walked out of the bathroom and saw his brother heading for the kitchen with the stack of boxes. Gabe laughed and nodded.

“Yes, and this time I got two boxes so I get more than just a single piece.”

“Sorry, they’re just really good.” Cas said as he entered the kitchen. He made a beeline straight for the familiar shape of the breadstick box.

“I know, which is why I’d like some.” Gabe nudged his brother who grinned at him.

“So, was it the same delivery guy?” Cas asked.

“Yep. I was right, he is a government major, except he’s doing a double major in education as well. He’ll be teaching at the high school this next school year.” Gabe opened up his pizza and pulled out a slice. Cas looked up at him, his blue eyes bright with interest.

“Oh? And have you asked him out yet?”

Gabe rolled his eyes. Sometimes his brother really didn’t get it.

“No, I did not. He’s twenty two. I’m thirty four. But _you_ could ask him out.”

Cas cocked one eyebrow as he chewed on a bite of the breadstick in his hand.

“He’s gorgeous, Cassie. Tall, broad shoulders, long eyelashes, the greenest eyes. Looks like he walked off the pages of a magazine. Much like yourself.”

Cas leveled him with a bitch face that just made him grin. Cas didn’t see how good looking he was, but everyone else certainly did.

“You know it’s true. This is an argument you won’t win.”

“Whatever.” Cas rolled his eyes and stuffed more of his breadstick in his mouth. “So, you going to order again soon?”

Gabe grinned. Oh yeah, baby brother was interested…

~~~~~~~~~~~~~~~~~~~~~~~~

Over the next two weeks Dean found himself making no less than four trips out to deliver to the Novak residence, and every single time there was something written in the instructions box.

_List the planets in order from closest to the sun to the farthest_

_Do you like Kermit the Frog better, or Miss Piggy?_

_What is the definition of socialism?_

_Tell me you like my shirt_

That one had been interesting because Professor Novak had answered the door in the most obnoxious Hawaiian shirt Dean had ever seen, and it had been an outright lie to say he liked it. Fortunately his professor agreed and asked his real opinion of it. Dean told him it honestly looked like pineapples had thrown up all over it. Now he was heading out to their place again, but today’s instructions made him squirm. He was supposed to tell the man he was pretty. Not handsome, not attractive, not sexy (which personally, he didn’t think the man was), just…pretty. That was going to be awkward. He climbed the stairs to the apartment and tried to steady his nerves before he knocked. While he thought his professor was a pretty cool guy, he did not, in any way, find him physically attractive. Still, for the ten dollar tip, he’d lie through his teeth. Taking a deep breath, he knocked.

“Cassie! Door!”

Cas looked up from his spot on the couch where he was watching Dr. Sexy. Gabe had gone into the bathroom almost twenty minutes ago and still wasn’t out. He hadn’t really been feeling well most of the day.

“Do you want me to just sign your name to the receipt?” he asked as he got up.

“Yes! And leave Dean a ten in cash as a tip, he deserves it!” Gabe called back. Cas smoothed down his shirt and headed for the door. Until now his brother had handled the pizza delivery because he had to sign the receipt. He patted his pocket to make sure he had his wallet before walking over to the door and opening it.

“Uh, hi.” The man on the other side of the door’s eyes widened when they fell on Cas. Cas stared back.

“I have your delivery?” The man held the boxes up and Cas forced himself to look at them, but only for a moment before he was staring back into the greenest eyes he’d ever seen in his life.

“You’re Dean?” he asked. The other man smiled and nodded.

“Yes, that’s me.”

Cas suddenly felt incredibly shy. He dropped his eyes as he accepted the boxes, setting them on the table just inside the door.

“My brother speaks very fondly of you.” 

“Oh. I’m glad? I mean, he’s my favorite professor this semester. He makes learning fun.” Dean smiled and Cas found the man even more attractive at the small gesture.

“He’s the reason I wanted to teach. He always did make learning fun, even when I was little,” Cas found himself saying. There was an awkward silence for a moment before Dean thrust a receipt at him.

“I’m going to be teaching. Not at the university but at the high school.” Dean said as he watched Cas lean the paper against the wall and sign it. He most certainly was _not_ staring at the strip of tan skin peeking out from under the man’s tee shirt. 

“I’m Cas, by the way,” Cas said as he handed Dean back the receipt.

“That’s a much nicer name than Cassie,” Dean said with a laugh. Cas’ cheeks flushed slightly and he gave a shy smile.

“Oh, that’s been his nickname for me since I was born. I hate it if anyone else tries to call me that, but I’m used to it from him.”

There was another awkward moment before the smile on Dean’s face faded and he stepped back. “I, uh, have another delivery, but it was nice talking to you.” 

He got a few steps down the hall before Cas realized he hadn’t tipped the man.

“Wait! Your tip!’

Dean stopped and looked back at him, those green eyes wide once again. He took a few tentative steps back towards the apartment door. Cas pulled his wallet out and looked inside. 

“I only have a twenty,” he said, more to himself than to Dean.

“I have change,” Dean told him. Cas smiled as he fished the money out of his wallet and held it out.

“Y-you’re pretty,” Dean blurted. His cheeks were incredibly red, but Cas was too shocked by his words to respond. He stood there just holding the money out. Dean reached forward with one shaky hand to pluck it from his fingers. He was reaching into his pocket to find bills to break it when Cas held up a hand.

“No, you keep it.”

Dean looked up, his cheeks still burning, and gave a short nod. “T-thanks.” He turned to leave but paused a moment, turning back to look again at Cas. “I, um, meant that. Goodnight!” 

Cas watched as the man practically fled the building. He didn’t remember closing the door or leaning back against it until his brother was suddenly in his face, waving a hand to get his attention.

“What’s your problem?” Gabe asked. Cas blushed. Hard.

“H-he…told me I was pretty!” It came out as a whisper. Gabe blinked and then the corners of his mouth tilted upwards into an amused grin. 

“Holy hell, he actually said it?”

Cas frowned. “You…put him up to that?”

Gabe doubled over laughing. He ended up grabbing on to the edge of the couch as he tried to get himself under control. When he finally did, he looked up at his brother with a sober expression.

“It was meant for me. I expected to answer the door. I’ve been giving little off the wall instructions like that since the first time I ordered with them. It’s sort of a running gag by now. I didn’t think he’d say it to you. What else did he say?”

Cas felt his cheeks getting warm again. He hadn’t blushed this much since he was a kid!

“He, um…said he meant it.”

Gabe fist-pumped the air. “So he _does_ like guys! I thought he might! And he likes _you_!”

Cas grabbed the boxes and started for the kitchen. “That was embarrassing, Gabe. Especially for Dean. I’m sure he won’t want to deliver to us anymore after that.” 

To Gabe it sounded like his brother was pouting.

“I can fix that, you know,” Gabe said. Cas looked up from the box of breadsticks he’d just opened and waited for him to elaborate.

“I’ll talk to him tomorrow after class.” 

Cas frowned. “Don’t embarrass him further, it’s not nice.”

“I promise I won’t.” Gabe dragged his index finger across his left pec in the shape of a cross. As they sat down to eat he looked over at his younger brother. Cas appeared to be lost in thought.

“He’s attractive though, isn’t he?” 

Cas was definitely blushing again, but he nodded. “He really is. You weren’t kidding about his eyes, though you forgot to mention the freckles.”

Gabe smiled around a mouthful of pizza. He chewed quickly and swallowed. “If I can get him to deliver again, you should ask him out.”

Cas looked up briefly before looking away again. “Really?”

“Absolutely. I mean seriously, when are you going to meet another man even half that attractive, or intelligent?”

Cas shrugged but eventually nodded in agreement.

“Plus he thinks you’re pretty,” Gabe teased.

“Oh, shut up.”

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Dean fell into the driver’s seat and dropped his head onto the steering wheel. Did he really go through with that? Clearly Cas hadn’t expected him to say it. That was another gag from Professor Novak that apparently his incredibly HOT brother got caught in the middle of. But seriously, the dude was gorgeous! He did have one more delivery scheduled, so he quickly made it. College students again, so no tip. Figured. He drove back to turn in his bags so he could go home. Hopefully the following day wouldn’t be weird when he had to sit through Professor Novak’s class.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Gabe watched as his students filed into his class. So far, Dean had not come in. He had a lecture planned on ethics vs. morals in politics. It was bound to be a heated discussion, and he was really looking forward to it. Dean came walking in last with a big guy Gabe remembered as Benny and a skinny little redhead. Celeste was her name, but she liked to be called Charlie. They were talking and from the motions Charlie was making, Gabe suspected she was talking about a video game. They took their usual seats together at the back of the room. 

The class discussion was indeed entertaining, though he had to shut several people down before they ended up actually fighting. Dean and his friends participated, especially Charlie, who had an opinion about everything. As the class drew to a close Gabe dismissed each student one by one as he handed out the last test they had taken. He had saved Dean’s for last on purpose. When he finally called Dean down, they were alone.

“You did quite well, Dean. Your answers always impress me. Do you think you’re ready for the final?” he asked as he handed the paper over. Dean took it, smiling when he saw the 100% mark in the corner.

“I’ve been studying hard, so yeah, I think I’m prepared.”

“That’s good. In case you forgot from the first day of class, the final counts for thirty percent of your grade, so you definitely want to be prepared for it.” 

Dean nodded. “I will be.”

Gabe licked his lips and looked up at the man. “Hey, I’m sorry if you were embarrassed the other night. I hadn’t exactly meant for my brother to answer the door. I’m often told that I have a weird sense of humor, and I was just playing around.”

Dean waved his apology off. “It’s fine. I expected it to be you too, but I didn’t think I’d get the tip if I didn’t follow the instructions, so it just sort of slipped.”

“You...” Gabe frowned. “I always tip, Dean. So does my brother. The instruction section was all in good fun. He had no idea I was even doing that.”

Dean looked down at his boots so his professor wouldn’t see his cheeks turning red. “Oh.”

“I’ll say though, you certainly made his night. He asked me if we were going to order from you guys again.”

Dean tried to hide his smile but he couldn’t. He ran his lower lip between his teeth as he looked up again. “Yeah?”

Gabe smiled and nodded. “Oh yeah. I don’t think anyone has ever told him he’s pretty.”

Dean blushed harder. Gabe found it adorable.

“And meant it.”

Dean groaned and pinched the bridge of his nose. “I still can’t believe I said that part.”

“Did you really mean that?” Gabe asked.

“This is weird. He’s a teacher, your _brother_.”

Gabe sighed deeply. “And he’s twenty five, way the hell too attractive for most men, and he thinks you’re hot. And did you forget that in another couple of months you will be a teacher too?”

Dean’s hand fell away, and he looked up in surprise. “He thinks I’m hot?”

“Yes, and I think you like him too. I’m going to go out on a limb and say you’re into guys. Am I right?” Gabe asked.

“Yeah, I’m bi. I mostly date men though. And yes, he’s…very attractive.”

So Gabe had been reading him right. “He’s gay. And you were all he could talk about last night. Don’t tell him I said that though, he might disown me.”

Dean snickered, “I won’t.”

“So if we order again, you won’t be too embarrassed to deliver, will you?”

Dean shook his head. “No, I’ll definitely deliver it.”

Gabe grinned. “Good. Well, I’m sure you have classes to get to. I’ll see you Friday.”

“Yep. Bye, Professor Novak.”

“Goodbye, Dean.”

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

“I fixed it. He’ll still be delivering our orders,” Gabe said as he marched into the office his brother shared with two other associate professors. At the moment Cas was the only one in there, til his brother walked in.

“What did you do?” Cas looked up from his lunch of leftover pizza and frowned. “Please tell me you didn’t do something to embarrass the poor man. Or me, for that matter.”

“Not at all. But I learned that he is bi, leaning more towards men than women, and he finds you _very_ attractive. Don’t tell him I said that though,” Gabe said as he sat down in the seat across from his brother. Cas was staring at him with a look of utter disbelief. 

“He did _not_!”

“Oh, he did! I think you should ask him out.” Gabe crossed his arms and gave his trademark smirk. “He’s hot, there’s no denying it.”

Cas rolled his eyes, a common reaction when it came to dealing with his brother.

“Looks aren’t everything. He does seem very nice though.”

“He is, and I can tell you, he’s one of my smartest students. Doesn’t rise to the bait when others with hotter tempers get overzealous during discussions. Instead he tends to either be the voice of reason or he’ll play devil’s advocate. He’s certainly making the class more interesting.” Gabe had to admit, he didn’t usually play favorites, but Dean was one of the best students he’d ever had. Charlie was a close second. “I think he’s going to be an excellent teacher.”

“So, how would I go about asking him out? I mean, assuming he’s really interested.” Cas was failing miserably at trying to sound disinterested. Gabe knew him all too well.

“I…have an idea.”

~~~~~~~~~~~~~~~~~~~~~~~~~~~

Dean was looking forward to the end of his shift. He’d had a long week, and he was tired. All night long he’d been delivering to college students. People were rude, they pranked him, and after twenty some deliveries, he’d made a lousy twenty two dollars in tips. It was frustrating. As he walked back in the shop he heard Jo calling his name.

“Dean! One last order tonight, and then you’re off. I think you’ll like this one.” 

He trudged over to the counter, and she handed him a single pizza box and one box of breadsticks along with the order slip. 

“Thanks. I’ll just drop the bags off tomorrow if that’s ok,” he told her.

“That’s fine. Or bring them with you to work Saturday,” she said.

“Alright. Goodnight, Jo,” he said as he started for the door.

“Goodnight, Dean.”

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Out in the car Dean had to stifle a yawn as he slid in behind the wheel. He set the boxes on the passenger seat and looked at the order slip. The corners of his mouth twitched and began to rise up into a smile when he saw the address. It was Professor Novak’s order. A small gasp escaped when he read the delivery instructions though.

_Join me for dinner? C~_

Suddenly he was wide awake. 

“Dinner?”

He couldn’t procrastinate or the pizza would get cold. Then it would be coming out of his paycheck. As he drove he tried to get his heartbeat to calm down. It had said C, not G, after the dinner invitation. Did that mean Professor Novak’s brother Cas was really interested? His stomach did a flip just thinking about it.

As always the drive was short and soon he was climbing out of his car with his insulated bag. He went inside, climbing the stairs to the second floor. The path was now very familiar to him, and thirty seconds later he was standing outside the apartment. He took a shuddering breath before he knocked. It didn’t take long before he could hear footsteps, and then the door was opening. He found himself face to face with Cas.

“Uh, hi.” He suddenly felt very shy. Cas smiled.

“Hello, Dean.” 

Dean unzipped the bag and removed the two boxes. “Didn’t order as much tonight.” 

Cas smiled wider. “You’d be correct. Gabe is not here this evening.”

Dean shifted his weight from one foot to the other, a nervous habit since childhood.

“S-so you wanted me to have dinner with you?” 

“I…yes, if you don’t have any more deliveries. Only if you want to, of course.” 

Dean stopped fidgeting and smiled wide.

“I’d love to.”

**Author's Note:**

> So maybe I copied a bit off the Domino's menu. I happen to love their breadsticks. And they do have a section to leave instructions for the driver, not that they ever actually read them, lol. But I thought this prompt was too cute to pass up.
> 
> This makes it officially 100 fanfictions that I have written. I feel like there should be some confetti, but I'm too lazy to go get some, lol. I just hope you all enjoyed it. I like Gabe here, shipping his brother with the pizza guy, lol. Leave a comment and a kudos, and thanks for reading!


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